


10 Things I Hate About You

by southtrash



Category: Once Upon a Time (TV)
Genre: F/F, F/M, Humor, Romance
Language: English
Status: In-Progress
Published: 2020-11-17
Updated: 2020-11-20
Packaged: 2021-03-09 21:02:19
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 7,006
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/27612490
Author URL: https://archiveofourown.org/users/southtrash/pseuds/southtrash
Summary: OUAT take on a classic. Mild differences from the original. Entertaining read if you give it a chance. Emma and Henry are siblings. Emma/Regina story with some Violet/Henry, Robin/Marian if you squint. Don't like, don't read. I do not own 10 Things I Hate About You or Once Upon a Time.
Relationships: Evil Queen | Regina Mills/Emma Swan, Henry Mills & Violet
Comments: 5
Kudos: 15





	1. Chapter 1

Enjoy.

**10 Things I Hate About You**

Henry Swan stared at the guidance counselor before him. She was older, with a sense of bitterness he couldn't deny. He glanced down at the golden nameplate that sat on her desk: _Miss_ _Eugenia Lucas._

She chewed the gum in her mouth loudly, as she stared at the boy before her with what could only be described as disdain with a mixture of curiosity.

However, he couldn't dwell on it, as she evidently began to speak,

"So, Henry, you were at the top of your class at your last school, why the sudden move to a public institution?"

"Well my dad-"

"That's enough," she cut him off, with a wave of her hand, truly not caring for the answer. "I'm sure you won't find Storybrooke High any different than your old place of instruction. Private school, public school. It's still all the same little asswipe shit-for-brains everywhere."

Henry's eyes widened comically. "Excuse me, did you just say-" he looked around the room, to make sure this wasn't some sort of trick. "Am I in the right office?"

Miss Lucas just stared blankly. "Not anymore you're not. Now get out of here. I've got deviants to see and a novel to finish!" she waved her hand towards the door, as she slid her laptop closer to herself and began to type.

"Okay," Henry said awkwardly as he walked out the room. "Thanks."

He shook his head at the absurdity of the counselor and looked out into the waiting room, where he recognized a familiar face. "Emma!"

The blonde in question raised her eyebrow and looked around the empty room before speaking, "Henry, I told you not to talk to me at school, mom and dad wouldn't want you to be labeled as a bad seed."

Henry rolled his eyes. "Oh come on, I think I have the right to speak to my own sister."

"Yes well, they had _you_ going to that private school for a reason kid," she said with a weak smile and a shrug. "If it wasn't for dad getting laid off, you'd still be over there with the goody goody overachievers, not here with me."

He recognized the hurt in his older sister's eyes immediately. He knew it bothered her to no avail the amount of effort their parents made to keep him out of trouble, whereas she couldn't seem to stay out of it. "Emma I-"

"It's cool Hen," she cut him off, void of emotion. She pointed her fingers to the guidance counselor's door behind him. "Now if you don't mind, I got a date with Miss Lucas."

The boy watched her go with a sigh.

-TTIHAY-

"Ms. Swan. I see we're making our visits a weekly ritual."

Emma smiled, charming as ever. "Only so we can have these moments together. Should I get the lights?"

Miss Lucas shook her head at the girls immature antics. "Oh very clever," she glanced down at the incident report on her desk. "Says here you exposed yourself in the cafeteria?"

The blonde laughed. "I was joking with the lunch lady. It was a pink grapefruit."

"Grapefruit?" she glances down suspiciously at the girl's pants. "Aren't we the optimist? Next time keep it in your pouch! Now get out of here."

The blonde grinned, gave the older woman a salute, and walked out of the room.

As soon as she heard the door click shut, Miss Lucas looked back to her novel in progress and pondered before typing and reading out loud, "... then she exposed her pink grapefruit to his feasting eyes…"

-TTIHAY-

Henry walked down the halls of Storybrooke High, dodging energetic teenagers of all genders and sizes, before he was stopped by an upperclassmen. "Whoa there," he says, slightly out of breath from trying to catch up to the boy. "My name is Robin Locksley. Junior. I'm supposed to show you around."

"Oh hi!" said a relieved Henry. "Thank god! You know, I was expecting to be shown around by one of those A/V geeks."

Robin blushed. "Oh yeah, totally. I know what you mean."

A student passed, pushing a cart full of audio/video equipment. "Hey Robin, where should I put the-"

With a clearing of his throat, Robin ignored the question and pushed Henry by his shoulders further down the hall, away from the offending student. "Anyway, Henry, here's the breakdown," he pointed towards a group of jocks and cheerleaders ahead. "Over there you've got your basic beautiful people. Unless they talk to you first, don't bother."

Henry looked bewildered. _Is this really what public school is like?_ "Wait. Is that your rule or theirs?"

The junior shook his head at the new kid's ignorance and held a finger up. "Watch," he turned and tapped a random jock on the shoulder. "Hi there!"

The jock scowled. "Geek," and kept on walking.

Robin shrugged in indifference.

"Oh my god," Henry gaped, catching sight of a petite brunette goddess. "What group is she in?"

"The 'don't even think about it' group," Robin laughed, patting his new friends back. "That's Violet Mills. A sophomore."

"I burn! I pine! I perish!" Henry said, poetically.

"Listen. Forget her," Robin advised. "She's got an incredibly uptight mother, and it's a widely known fact that the Mills sisters aren't allowed to date."

_Maybe I can change that,_ Henry thought with a wishful smile.

-TTIHAY-

"Okay then. What did everyone think of _The Sun Also Rises_?" the professor asked his room full of bored seniors, and smiled at the hand that was raised. "Yes, Mary?"

"I loved it, Mr. Hopper," was her bubbly response. "It was sooo romantic."

He smiled at his student, while noticing the scowl on another. "Regina? You seem to disagree with Mary's assessment, what's your take?"

Regina rolled her eyes. "Hemingway is _not_ romantic," she snorted out, ignoring the outraged gasp from Mary. "He was an abusive alcoholic misogynist who squandered half his life hanging around Picasso trying to nail his leftovers."

"As opposed to a bitter self-righteous hag who has no friends?" came a male retort, from a seat behind the brunette girl, causing her to fume in her seat.

"Pipe down, Killian," Mr. Hopper said, with forced patience. He was all for constructive criticism, but sometimes Killian Jones grated his nerves.

"I guess in this society being male and an asshole makes you worthy of our time," Regina added, sarcastically. "What about Sylvia Plath or Charlotte Bronte or Simone de Beauvoir?"

Suddenly the door to her left flew open, and Emma stood at the doorway with a grin, "What'd I miss?"

"The oppressive patriarchal values that dictate our education," Regina answered, blandly.

"Oh, good," Emma said brightly, before turning around and leaving the class again.

Mr. Hopper flustered at the sight "Hey!"

Killian laughed. "Uh, Mr. Hopper? Is there any chance we could get Regina to take her Midol before she comes to class?"

_Okay, that's enough_ , the professor thought as he pushed his glasses up his nose and stared his student down. "Someday you're gonna get bitch-slapped Mr. Jones, and I'm not gonna do a thing to stop it. And Regina. I want to thank you for your point of view."

Killian glared at his teacher, while Regina smiled to herself smugly.

Mr. Hopper noticed, and continued, "I know how difficult it must be for you to overcome all those years of upper middle class suburban oppression. It must be tough."

The girl's smile deflated just a little, as she was chastised. "Anything else?" she said, bitterly.

_The attitude on this girl. These kids are just on a mission to annoy me today_ , he thought, gaining some boldness. "Yeah. Go to the office. You're pissing me off."

Her jaw dropped. "What?! Mr. Hopper!'

"Later!" Mr. Hopper said, done with her presence.

Regina huffed as she gathered her things, hitting Killian's face with her books on the way out.

-TTIHAY-

Miss Lucas sat in front of her laptop, working tirelessly on her novel, as she read it out loud, " _Undulating with desire, Adrienne removes her crimson cape...excitable, stiff and_ -" she stopped, as she came up short. "Belle!" she called out to her student assistant. "What's another word for engorged?!"

Regina approached the door, having heard the question. "Tumescent?"

"Perfect!" the woman exclaimed, typing the word in, then looking up at the brunette with a raised eyebrow. "So I hear you were terrorizing Mr. Hopper's class. Again."

"Expressing my opinion is not a terrorist action."

"The way you expressed your opinion to Neal Gold?" Miss Lucas retorted. "By the way, his testicle retrieval operation went quite well, in case you're interested."

The girl tried to hide her smirk, but failed while raising his hands in defense. "I still maintain that he kicked himself in the balls."

Miss Lucas rolled her eyes, used to the feisty brunette. "The point is Regina…" she began. "People perceive you as somewhat…"

"Tempestuous?"

"'Heinous bitch' is the term used most often," the older woman corrected with a pointed look. "You might want to work on that. Thank you."

Regina begins to exit the room. "As always, thank you for your excellent guidance. I'll let you get back to Reginald's quivering member."

The door clicked shut, leaving Miss Lucas alone with her thoughts.

"Quivering member...I like that."

-TTIHAY-

Killian Jones and his band of goons stood outside the courtyard, observing the nearest eye candy in appreciation.

"Virgin alert," his friend Smee said, tilting his head in the direction of the girls who were about to walk by them.

Killian smirked as he eyed them, one in particular though. "Looking good, Violet," he complimented as she passed by.

Violet smiled at him in acknowledgement and turned to her friend Ariel with a giggle as they continued walking.

"She's out of reach, even for you," Smee laughed.

"No one's out of reach for me," Killian answered smugly.

"You wanna put money on that?"

"Money, I've got...This...this I'm going to do for fun."

-TTIHAY-

Henry glared at the guy from across the courtyard who was just ogling the girl of his dreams. "Who's that guy?"

"Oh that's Killian Jones," Robin answered. "He's a jerk off. And a model."

"He's a model?"

Robin nodded. "Mostly regional stuff. He's rumored to have a tube sock ad coming out. It's supposed to be pirate themed."

That made Henry laugh. "Really?"

"Really."

At that moment, Violet and Ariel walked past the two boys, not paying them any mind. However, Henry was suddenly distracted all over. "Man, look at her."

Robin looked, but was not seeing the same thing his friend saw. "Is she always so vapid?"

"How can you say that? She's totally-"

"Conceited?"

"What are you talking about?" Henry exclaimed, not believing him for a second. "There's more to her than you think. I mean, look at the way she smiles. And look at her eyes. She's totally pure. I mean, you're missing what's there."

Robin disagreed. "No Henry. No. What's there is a snotty little princess wearing a strategically planned sundress to make guys like us realize we can never touch her, and guys like-" he stopped, seeing Killian walk up to the girls. "Killian realize they want to. She, my friend, is what we'll spend the rest of our lives not having. Put her in the spank bank. Move on."

"No," came the defiant response.

"Move on, Henry."

"No, you're wrong about her. I mean, you know, not about the spanking part," Henry admitted sheepishly, "But the rest. You're wrong."

"Oh I'm wrong? You wanna take a shot? Be my guest. She's actually looking for a French tutor," Robin added teasingly.

"Are you serious?" Henry said with an open mouthed grin. "That's perfect!"

"You speak French?" Robin said incredulously.

"Well, no. But I will."

-TTIHAY-

Regina and her best friend Marian walk towards her car in the school parking lot in a deep-rooted conversation, before they are interrupted by Killian's sports car as it pulls up beside them. "Hey your little Rambo look is out, Reg. Didn't you read last month's Cosmo?" he said.

"Run along," she answered, barely paying him any mind, pulling Marian along with her as they keep walking.

Further ahead of them, stood Violet and Ariel, immersed in a conversation of their own.

"I know you can be overwhelmed. You can be underwhelmed. But can you ever just be whelmed?" Ariel questioned, twirling her hair with a finger in clear distress.

Violet seriously pondered the question. "I think you can in Europe?"

Killian pulled up beside them. "Hey ladies. Would you sweet young things like a ride?"

They look at each other briefly, shrugging with grins as they climb into his car. "Alright, careful on the leather," he admonishes.

Across the way, Regina and Marian watch the scene unfold, as they sit in Regina's car.

"Well that's a charming new development," Marian stated.

"It's disgusting."

As Regina is about to put her car into drive, Robin motor scooter's his way in front of her car by accident, making her roll her eyes and shout, "Remove head from sphincter, then drive!"

Robin huffs, regains control of his scooter, and scoots over to where Henry was standing.

"You alright?"

"Yeah, just a minor encounter with the shrew," Robin explained, why he ever had a crush on that girl in freshman year is beyond him. "Your girlfriend's sister."

Henry's eyes widened. " _That's_ Violet's sister?"

"Mhmm, the mewling, rampalian wretch herself," Robin nodded, before waving his goodbye to his new friend, "Stay cool bro."

Henry, distracted, barely muttered his response as he tried to figure out how to utilize this new information he has received to his advantage.

-TTIHAY-

Regina sat in her living room, as she rifled through some emails on her laptop. Looking up to the doorway when she heard footsteps come nearer. Smiling when she saw her loving, albeit obsessively overprotective mother. Cora Mills.

"Hello Regina," she smiled back. "Make anyone cry today?"

She grinned. "Sadly no, but it's only four-thirty."

That response made her mother grin proudly. She was about to respond but stopped at the sound of her other daughter, "Hello mama."

She hugged Violet tightly. "Hello precious."

"And where have you been?" Regina snarked at her younger sister.

Violet glared, pulling away from her mother so she could plop down on the couch. "Nowhere."

Cora ignored her always bickering daughters, as she sorted through their newest set of mail, squinting as she pulled one of interest, "What's this? It says Sarah Lawrence?"

Regina ran across the room, snatched the letter from her mother and tore it open. "Oh my god! I got in!"

Cora smiled tightly. "Honey, that's great. But isn't Sarah Lawrence over seven hours away?"

"Thus the basis of its appeal."

"I thought we decided you were gonna stay here like me. Be a Husky?" the older woman said, hopefully.

"No," Regina sighed. " _You_ decided."

"Oh okay. So you just pick up and leave, is that it?" Cora exasperated.

Violet perked up. "Let's hope so."

Regina glared, but then smiled remembering the dirt she had, "Ask Violet who drove her home."

"Do not change the subject-" Cora stopped, processing the words. "Drove? Who drove you home?" she turned to her youngest.

"Now don't get upset, mama. But there's this boy…"

"Who's a flaming imbecile," the older sister remarked.

"...and I think he might ask me…"

"Please," Cora rolled her eyes, evidently it's a genetic trait. "I think I know what he's going to ask you. And I think I know the answer: No. It's always no. What are the house rules? Number one, no dating until you graduate. Number two, no dating until you graduate. That's it."

"Mama, that's so unfair," Violet whined.

"Alright you wanna know what's unfair? This is for you too," the mother said, pointing at Regina. "This morning I delivered a set of twins to a 15 year old girl. Do you know what she said to me?"

"I'm a crack-whore who should have made my sleazy boyfriend wear a condom?" Violet said sarcastically.

Cora paused, somewhat impressed with the response but shook her head. "Close. But no. She said, 'I should. Have. Listened. To my mother.'"

"She did not," Violet argued.

"Well that's what she would've said if she weren't so doped up," Cora replied, matter of factly.

"Can we focus on me for a second please? I'm the only girl in school who's not dating."

The mother was quick to shoot down the complaint smugly with a point of her finger, "Well that's not true. Your sister doesn't date."

"And I don't intend to," Regina stated, smirking.

"And why is that again?" Cora said, pleased.

"Have you seen the unwashed miscreants that go to that school?"

Violet gaped incredulously. "Where did you come from? Planet Loser?"

"As opposed to planet 'look at me! Look at me!'?" the brunette threw back, while flipping her hair mockingly.

Cora saw an opportunity and waved her hands about to stop her children's bickering. "Okay, here's how we solve this one. Old rule out...new rule: Violet can date..." she began. Violet brightens at the statement. "...When Regina does."

The younger girl scowls once again, "But she's a mutant! What if she never dates?"

"Then _you'll_ never date," the mother answered immediately with a grin. _Ooh I like that._ "And _I'll_ get to sleep at night. The deep slumber of a mother whose daughter's aren't out being impregnated or felt up."

Satisfied with the new rule changes, Cora turns to exit the room, but pointing a finger at Regina as she did so. "We'll talk about Sarah Lawrence later."

"Fine."

"But mama!" Violet starts.

"I gotta go, sweetie," Cora says, pulling her jacket off the rack and heading out the front door.

Now alone with her sister, Violet turns her desperation over to her, "Can't you find some weirdo to take you to the movies so I can have just one date?"

"I'm sorry," Regina replied, quite unapologetically. "Looks like you'll just have to miss out on the witty repartee of Killian 'eat me' Jones."

"You suck."

-TTIHAY-

Henry sat nervously in the tutoring room, as he awaited Violet's arrival. He was successfully scheduled to tutor her in French.

Abruptly Violet sat before him, "Okay, can we make this quick? Belle and Gaston are having an incredibly horrendous public break-up on the quad. Again."

"Oh yeah, um," Henry started, "I thought we could start with pronunciation, if that's alright with you."

"Not the hacking and gagging and spitting part. Please."

He nodded, working up the courage for his next sentence, "Well, there is an alternative… French food? We could eat some together. Saturday night?"

Violet looked amused. "You're asking me out? That's so cute. What's your name again?"

Embarrassed, he continues, "Uh Henry… Listen, I know that your mom doesn't let you date. But I thought that if it was for French class it-"

"Oh, wait a minute, Hank-"

"Henry."

She ignored him. "My mom actually just came up with a new rule. I _can_ date, when my sister does."

"You're kidding!" he smiled. "Well let me ask you, do you like sailing ? 'Cause I read about this place that rents out boats-"

"A beaucoup problemo, Han. In case you haven't heard, my sister's a particularly hideous breed of loser."

He stopped, contemplating. "Oh yeah. I noticed she's a little antisocial. Why is that?"

Violet shrugged. "Unsolved mystery. She used to be really popular, and then it was like...she got sick of it. Or something. There is a bet as to why, but I'm pretty sure she's just incapable of human interaction," she paused then shrugged. "Plus, she's a bitch."

"Well yeah, but I'm sure, you know, that there's lots of people who wouldn't mind going out with a... difficult woman… it would be like extreme dating."

"You think you could find someone that extreme?" Violet asked, not believing it to be true.

Henry grinned. "Yeah, sure, why not?"

-TTIHAY-

"You said what?" Robin practically yelled.

"I'm gonna find a date for her sister," Henry shrugged. Scanning the quad for possible candidates. "Any ideas?"

"It is pointless, no one will go out with her. They'd have to literally have no care for their own life. Or have a criminal background."

That gave Henry an idea. "Come on."

"Where are we going?"

"You'll see."

-TTIHAY-

The duo entered the current Biology lab that was in progress, Henry pointing at the blond girl sitting in the back of the class with her lab partner, as they hacked away at their dissected frogs.

"What about her?" Henry asked, innocently.

Robin studied the girl, watching as she pulled out a butterfly knife and impaled her frog violently with it. He instantly paled, "Her? No, no. Don't look at her, okay? I know I said we'd need a criminal, but I was kidding," he continued. "I heard she lit a state trooper on fire. She just did a year in San Quentin."

Henry laughed. Is this what people thought of his sister? "Well if that's true, then at least we know she's horny."

"I'm serious, she's whacked. She sold her own liver on the black market for a new set of speakers," he exclaimed as loudly as he could without Emma hearing them.

The girl, still oblivious to their presence, took out a cigarette and used the Bunsen burner next to her lab partner to light it.

"She's our girl," Henry said confidently. If anyone could handle this Regina chick, it was his badass older sister.


	2. Chapter 2

**Author's Note** : I don't own OUAT or 10 Things I Hate About You. Thoughts are in italics. I just thought writing this would be a fun idea. Reviews welcome.

In this chapter we get some Regina/Emma interaction.

Enjoy.

**Chapter 2**

_I want to tell Robin she's my sister, but watching him fear her is just too funny,_ Henry thought as he watched Robin approach Emma during her Woodshop class, clutching a book to his chest for security purposes as he stepped nearer.

"Hi. How you doin? Listen, I…"

Emma stopped drilling through her block of wood to regard the boy in front of her blankly. She then grabbed the book out of his hands, took out her power tool, and drilled a hole straight through it.

She handed it back with a smile, then went back to what she was doing.

Robin glanced down at his now ruined book, rightfully scared. "Okay...later then…" then proceeded to practically run out towards his friend in the hallway. "Yeah, I don't know. She's terrifying. How are we going to get her to date Regina?"

Henry took a deep breath. "I'll ask her."

"Did you not see how that just went ?" Robin said, gesturing towards the classroom he just ran out of.

"I mean, yeah, that was embarrassing to watch," Henry admitted with a laugh. "But I'm sure she'll at least hear me out."

"Oh yeah? Why's that?"

"Emma is my sister," the younger boy finally admits.

"What?! This whole time, you could've just led with that," Robin ranted, outraged. "YOU'RE the one who wants to date little miss prissy, and I'M over here risking my life for you to ask your own sister to help you out. I swear, you underclassmen."

-TTIHAY-

"Please."

"No."

"Emma please."

"I said no."

Robin stared uncomfortably at the bickering siblings as he sat in their living room. He and Henry decided it best to wait for school to get out before they bombarded the girl with their favor, but it wasn't faring too well.

Emma and Henry were standing across from each other. Their body language speaking wonders on the situation, as the blonde girl's arms were firmly crossed and defiant, while the boy waved his arms about desperately.

"Oh come on Em-"

"Henry," she sighed. "I just don't see how this would benefit me. So no."

"But-"

"No," she said firmly, walking out of the room.

The silence that followed made Robin extremely uncomfortable. So he broke it instantly, "So now what?"

"I don't know," Henry answered, his mind working overtime trying to figure out a solution. "I mean, we could pay her? But we don't have any money."

Robin nodded, scrunching his face in thought. "Yeah, what we need is a backer."

"What's that?"

"Someone with money who's stupid."

-TTIHAY-

Killian sat with his buddies in the cafeteria as they crudely drew the female anatomy onto their food trays with magic markers. "Oh yeah, this is my best work yet."

Robin attempted to casually walk up to the group. "Hey friend, is that a fruit roll-up? Cause you don't see many-"

"Are you lost?" Killian asked, the threat clear in his voice.

"No, actually, I just came by to chat…"

"We don't chat."

Robin laughed nervously. "Well, I thought I'd run an idea by you. Just to see if you're interested."

"I'm not."

"Well, hear me out," he implored. "You want Violet, right? But she can't go out with you because her sister is insane and no one will go out with her, right?"

Standing to face the A/V nerd closely, Killian's eyebrow raised in mild interest, as he grabbed the other teen's face and began to draw on it with his marker. "Does this conversation have a purpose?"

"What I think you need to do is hire someone who will go out with her," he replied, closing his eyes as he felt the marker run across his face. "Someone who doesn't scare so easy."

Killian laughed, admiring his work as he pulled his marker away. "And who would that be?"

Emma's laughter cut into their conversation, making both boys turn to her direction where she was currently sitting with her friend Ruby. Ruby was shaking her head in disapproval as the blonde was inconspicuously making a shiv out of her school-issued spork.

Robin gestured his head in her direction suggestively.

"That chick?" the bully said incredulously. "I heard she ate a live duck once."

"Everything but the beak and feet," Robin affirmed, confidently. "Clearly she's a solid investment."

"What's in it for you?"

Hands held up in surrender. "Hey. I'm walking down the hall and say hello to you, just say hello to me."

"Yeah, I get it, you're cool by association," Killian said, sucking on his teeth a bit. "I'll think about it."

"Nice...I'll just get going then."

He quickly walked to the opposite side of the cafeteria where Henry stood, looking anxious. "Did it work?"

"He's going to think about it," Robin answered with a nod. "So now, we let him pretend he's calling the shots, while you can have your time with Violet."

Henry grinned. "Good idea," he paused, finally processing his friend's face. "Why do you have a dick drawn on your face?"

-TTIHAY-

Out in the Storybrooke playing field, the girl's soccer team is practicing, the cross country team is running laps, the marching band is going over cadences, and Emma and Ruby are subtly smoking cigarettes under the bleachers.

Taking a deep breath, Killian hypes himself up to approach the slightly intimidating pair. Deciding to just go for it, he ducks under the bleachers and stands before them as they stop to look at him.

"Hey, how ya doin?" he says, awkwardly. The two girls ignore him, taking another drag from their cigarettes. He cleared his throat and tried again, looking at Emma, "I had some great duck last night…"

Rolling her eyes, she finally answered, "Do I know you?"

Happy to get a response, he points out to the field, "See that girl?" gesturing to the brunette who was in the middle of kicking a soccer ball to her teammate.

Emma turns to look, and notices that it's the same girl Henry wanted her to go out with. "Yeah, what about her?"

"That's Regina Mills. I want you to go out with her."

Ruby bursts out laughing. "Is this guy serious?"

The blonde did not look impressed. _What is with dudes and not being able to get a girl on their own?_ "Not interested."

Getting frustrated, Killian continues, "Look. I can't take out her sister until Regina starts dating. You see, their mom's whacked out. She has this rule-"

"That's a touching story. It really is," Emma replied, sarcastically. "Not my problem."

"Would you be willing to make it your problem if I provide generous compensation?"

Thinking back to her conversation with her younger brother, she immediately knows he has something to do with this. _Guess he found a way for me to get something out of this. Alright. You win, Hen._ She smirks, "You're going to pay me to take out some chick?" smirking wider when he nods. "How much?"

"Twenty bucks."

Emma turns back to take another look at Regina, who just violently body checked another girl to the ground.

Killian winced, then concedes, "Fine. Thirty."

The blonde clicks her tongue, "Well let's think about this," she began to count things off her fingers. "We go to the movies. That's uh, 15 bucks. We get popcorn. That's 53. And, she'll want Raisinettes, right? So we're looking at about 75 bucks."

"This ain't a negotiation, love," he shook his head, not liking how this conversation was going. "Take it or leave it."

She laughs. "Alright, 50 bucks and we've got a deal, guyliner."

Killian smiles widely, handing her the money.

-TTIHAY-

"Great practice, everybody!"

The soccer team is being dismissed for the day, and began to walk off the field. Emma sees this from her place under the bleachers with a smile. Ruby had long gone, as she had to meet up with her boyfriend. So the blonde decided to wait out practice and attempt her first official conversation with Regina Mills.

Throwing her cigarette aside, she approaches the snarky brunette. "Hey there girlie. How you doing?

"Sweating like a pig, actually," Regina huffs out, wiping her sweat off with her jersey. "And yourself?"

Emma smiles, attempting to flirt. "Now there's a way to get a guy's," she stops, as Regina glares and amends her statement, "-or girl's attention."

"My mission in life," the brunette says, sarcastically. Then moves her hand to her hips. "But obviously I've struck your fancy. So, you see, it worked. The world makes sense again," with that she attempts to walk away.

However, the blonde is following closely behind. "Pick you up Friday then?"

Regina laughs, a little shocked that she hasn't scared this person away, and a little annoyed. "Oh, right. Friday. Uh huh."

"Yeah, it'll be the night I take you places you've never been before," Emma said, wiggling her eyebrows suggestively.

"Like where? The 7-Eleven on Broadway? Do you even know my name screwgirl?"

_I like her, she's fun_. Emma smiled. "I know a lot more than you think."

"Doubtful, very doubtful," the brunette walked away briskly, leaving the blond girl standing alone.

-TTIHAY-

"We are so screwed," Henry said, it didn't look like Emma had much of a chance there. He and his friend had been scoping out the field from afar when they noticed Killian go up to his sister a little earlier.

"Hey, no hey," Robin soothed, he's put too much effort into this operation for it to fail. "I don't want to hear that defeatist attitude. I want to hear you upbeat."

Henry put on a fake smile. "We are so screwed!"

"There ya go."


	3. Chapter 3

**Summary for the Chapter:**

> A bit more Emma/Regina interaction in the beginning. Violet helps Henry get intel on what Regina is into.

**Notes for the Chapter:**

> I do not own OUAT or 10 Things I Hate About You.

**Chapter 3**

A few days later, following Emma’s failed attempt to take out the brunette beauty. Regina was walking out of a store only to find that same infuriating blonde leaning against her car. 

"Nice car,” Emma commented. “Vintage fenders.”

“Are you following me?” the brunette accused.   
  
Emma laughed, pointing behind her. “I was in the laundromat. I saw your car. I came over to say hi.”

“Hi,” came the bland retort.

“Not a big talker huh?”

“Depends on the topic. My fenders don’t really whip me into a verbal frenzy.”   
  
The blonde smiles, genuinely. “You’re not afraid of me, are you?”

This confuses Regina, “Afraid of you? Why would I be afraid of you?”

“Well most people are.”

“Well I’m not.”

“Well, maybe you’re not afraid of me,” Emma admitted, a slow smirk taking over her face. “But I’m sure you’ve thought about me naked, amirite?”   


“Am I that transparent?” the brunette gasps out, fanning herself. “I want you, I  _ need _ you. Oh baby. Oh. Baby,” she forcefully pushed the blonde out of the way so she could get into her car.

Emma watches on amused as she revs her car before backing out, only to be blocked by Killian’s sports car. He doesn’t care, as he stays blocking her, and exits his car.

“What is it ? Asshole day?” Regina yells out, throwing her hands up. “Do you mind?!”

“Not at all,” Killian says brightly, walking into a nearby store.    


This makes her set her face into a determined glare as she backs up quickly, effectively crashing her ‘vintage fenders’ into the door of her enemy’s car.

_ Not gonna lie,  _ Emma thought with a smirk.  _ That’s pretty hot. _

The aforementioned enemy immediately rushes out with his hands in his hair as he sees the damage, “You bitch!”   


Regina shrugged. “Woops?” before driving away.

\--------TTIHAY-------------

“Woops?!” Cora exclaimed, pacing as her eldest daughter sat calmly on the couch. “My insurance does not cover PMS.”

She inspected her fingernails. “Well, then tell them I had a seizure.”

The mother sighed, tiredly. “Is this about college? Are you punishing me because I want you to stay close to home?”

“Are you punishing me because daddy left?” came the cold reply.

“You think you could leave him out of this?” 

“Fine. Then stop making decisions for me.”

“I’m your mother,” Cora said defiantly. “That’s my right.”

Regina replied in shock, “So what I want doesn’t matter?!”

Her mother shook her head. “You’re eighteen, you don’t know what you want. And you won’t know what you want until you’re forty-five. And if you get it, you’ll be too old to use it.”

“I _ want _ to go to the school of my choice!” Regina ranted. “I  _ want _ you to trust me to make my own decisions. And I  _ want _ you to stop trying to control my life just because you can’t control yours.”

“Oh yeah? Well you know what I want?-” Cora began, but was cut off by her phone beeping. Sighing, she read the message, then looked back to her daughter with a sigh. “We’ll continue this later.”

“Can’t wait,” came the unenthusiastic reply.

  
\-------------TTIHAY----------------   
  


Emma whistled as she shut her locker, revealing Killian’s angry face as he glared at her. “When I shell out 50, I expect results.”

“Yeah, I’m on it,” she said, nonchalantly.

“Watching that bitch violate my car doesn’t count as a date.”    


She pulled a stick of gum out of its wrapper and put it in her mouth speaking as she began to chew, “I just upped my price.”

Killian laughed. “What?”   


“A hundred bucks a date,” she said. Popping her gum. “In advance.”

He shook his head, “Forget it.”

“Forget her sister then,” she said smiling cheekily.    


Killian thinks for a moment, and frustratingly pulls a fifty from his wallet. “You better hope you’re as smooth as you think you are, Swan.”   


Emma takes the money with a grin.

  
\--------------TTIHAY-------------------

Robin and Henry sat in his room as they listened to music. They both jumped at the sound of the bedroom door slamming open.

“I know what you did,” Emma stated, ignoring Robin and walking directly in front of her brother. “You got Killian Jones involved with your little Mills scheme.”

“I was desperate!” Henry exclaimed. “Plus, now you can’t say you won’t be getting anything out of it.”

“I’m just surprised you’re all falling over yourselves over this chick,” she said. “She have beer flavored nipples or something?”

“Don’t talk about her like that!” her brother said, beginning to get annoyed.   


Robin decided to interject. “Look, I think it’s safe to say Henry’s love for Violet is pure. Way purer than Killian Jones’s.”

Emma shrugged, pretending to be indifferent. “Look, I’m in on this for the cash. Jones can plow whoever he wants.”

Henry glared at her. “There will be no plowing!”   
  
She laughed as she ruffled his hair. “I’m just kidding.”

“It’s not funny.”

“Yes well, neither is this whole situation,” Emma answered. “So are you two gonna help me tame the wild beast?” referring to the sassy Regina.

“We’ll do some research,” Robin grinned. “We’ll find out what she likes.” 

Henry nodded. “Yeah! Hopefully we can get her to like you before Will Scarlett’s big party.” 

  
\---------TTIHAY--------------

In the halls of Storybrooke High stood Killian as he showed some glamour model photos to Violet. “Okay love, now this is important, which one do you like better?”

Violet glanced at the photos. They were literally the same. “Uh, the right one?” 

He glances at it and nods. “Yeah it's more…”

“Pensive?” 

“Damn, I was going for thoughtful,” he said, missing the roll of her eyes. “Anyway, you going to Will Scarlett’s thing on Friday night?”

That made her smile flirtatiously. “Yeah, I might.”

He grinned. “Good. You know I’m not gonna bother if you won’t be there.”

\---TTIHAY-----

Henry and Violet met up after school and were taking a walk around the campus, conveniently no one was around. 

“So have you heard about Will Scarlett’s party?” he asked shyly. 

Violet pouted. “Yes. And I really, really, really wanna go, but I can’t. Unless my sister goes.”

“Yeah I know,” he said. “I’m working on that. But so far she’s not going for the girl I got…”  _ maybe she’s not a lesbian? _ he thought. “She  _ is _ a ..?”   
  
“KD Lang fan?” Violet asked with a laugh. “Hell yes. I caught her making out with our neighbor Mallory a couple years back. Not to mention I found a picture of a half naked Scarlett Johansson in her drawer once. She’s definitely harboring same-sex tendencies.”   
  
“Okay then cool,” he smiled, his sister totally had a chance. “So Scarlett Johansson… is that the kind of girl she likes? Blonde and pretty?”

She shrugged. “I don’t know. All I’ve ever heard her say is that she’d die before dating anybody that smokes.”

Henry stored that away mentally. “Okay. Alright… what else?”

“You’re asking me to investigate the inner workings of my sister’s twisted mind? I don’t think so,” she scoffed.   
  
“Well nothing else has worked, we need to go behind enemy lines here.”

\---------TTIHAY-----------

A couple hours later, Henry watched as Violet went through her sister's room, looking for anything useful. “Okay here we go,” she said, walking over with a handful of things and giving them to the boy one by one, “Class schedule, reading list, date book, concert tickets, ah ha! Black panties!”

A little uncomfortable, Henry asks, “What does that tell us?”

“She wants to have sex some day, that’s what.”

He got flustered. “She could just like the color.”

She shook her head. “You don’t buy black lingerie unless you want someone to see it.”

“Oh,” Henry said, then boldly added, “So uh, can I see your room?”

Now Violet got flustered. “Uh no. A girl’s room is very personal.”

\------------TTIHAY------------------

  
“Why can’t we just talk to your sister at your house?” Robin said, as he worriedly looked around the biker bar Henry had dragged him to. “This place is gross. Don’t touch anything. You may get hepatitis.”

Henry rolled his eyes. “Emma won’t be back home till late. She always does this to piss off our parents. It’s just easier to come to her, trust me,” he looked around then pointed across the room. “She’s over there, come on.”   


Emma was playing pool by herself, but looked up when she sensed the two boys nearing her. She wasn’t surprised that they were there. Once Henry put his mind to something he didn’t waste any time. “So what you’ve got for me?” she asked them, before chugging the rest of her beer.  _ Fake IDs are the best,  _ she thought as she savored the taste of her beer..

“Just one question before we start,” Robin said curiously. “Should you be drinking alcohol when you don’t have a liver?”   
_   
_ “What?”  _ This dude is weird _ , she thought as she took out a cigarette to rest between her lips. She started patting her pockets as she looked for her lighter. 

“Nothing, nevermind,” Robin said, embarrassed. 

“First thing,” Henry started, getting down to business. “Regina hates smokers,” he said, taking the cigarette from his sister’s mouth and dropping it on the floor.

“You’re telling me I’m a,” she grimaced as if she had a bad taste in her mouth. “A  _ non _ smoker?”   
  
“Yeah but just for now,” Robin supplied, trying to get in the girl’s good graces.

“There’s another problem,” Henry continued. “Violet said that Regina likes ‘pretty’ types.”

Silence.

“Are you telling me I’m not pretty?” Emma asked, daring the boys to further insult her.

Robin, seeing another chance to kiss ass, rushed, “You’re very pretty! You’re gorgeous.”

“I wasn’t sure,” Henry said, holding his hands up.  _ Couldn’t hurt you to clean up a bit Emma. _ “Anyway, like I was saying, Regina likes: Thai food, feminist prose, and angry girl music of the indie-rock persuasion. Here’s a list of CDs she has in her room.”

Emma takes the list and reads it over. “So what? I’m supposed to buy her some noodles and a book and sit around listening to chicks who can’t play their instruments, right?”   


“Have you ever been to Club Skunk?” Robin asked.   
  
Emma made a face. “I can’t be seen at Club Skunk.”

“You have to,” Henry pleaded. “Her favorite band is playing there tomorrow night. She’s got tickets.”    
  
“Just assail your ears for one night,” Robin added, sympathetically patting Emma on the back. She glared at him and he stopped sheepishly.

“She has a pair of black underwear, if that helps,” Henry added.   
  
This made the blonde girl raise an eyebrow and smirk.


End file.
